JP6097216B2 - 電子デバイス用のゲート絶縁層 - Google Patents
電子デバイス用のゲート絶縁層 Download PDFInfo
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- JP6097216B2 JP6097216B2 JP2013526346A JP2013526346A JP6097216B2 JP 6097216 B2 JP6097216 B2 JP 6097216B2 JP 2013526346 A JP2013526346 A JP 2013526346A JP 2013526346 A JP2013526346 A JP 2013526346A JP 6097216 B2 JP6097216 B2 JP 6097216B2
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- polymer
- insulating layer
- gate insulating
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- 238000009413 insulation Methods 0.000 title claims description 7
- 229920000642 polymer Polymers 0.000 claims description 299
- 239000010410 layer Substances 0.000 claims description 216
- 239000000203 mixture Substances 0.000 claims description 199
- 239000000178 monomer Substances 0.000 claims description 106
- 239000000758 substrate Substances 0.000 claims description 65
- 239000000463 material Substances 0.000 claims description 52
- 229920003050 poly-cycloolefin Polymers 0.000 claims description 52
- 239000002904 solvent Substances 0.000 claims description 50
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 42
- 239000002318 adhesion promoter Substances 0.000 claims description 39
- 239000004065 semiconductor Substances 0.000 claims description 39
- 238000004132 cross linking Methods 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 33
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 20
- 238000000151 deposition Methods 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 239000003431 cross linking reagent Substances 0.000 claims description 14
- 125000000524 functional group Chemical group 0.000 claims description 14
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 14
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 13
- 239000003989 dielectric material Substances 0.000 claims description 13
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 13
- 239000004593 Epoxy Substances 0.000 claims description 11
- 229940114081 cinnamate Drugs 0.000 claims description 11
- 230000005669 field effect Effects 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 10
- 150000003923 2,5-pyrrolediones Chemical group 0.000 claims description 8
- 239000004971 Cross linker Substances 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000005647 linker group Chemical group 0.000 claims description 8
- 125000006850 spacer group Chemical group 0.000 claims description 8
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 7
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 7
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 7
- 229920002554 vinyl polymer Polymers 0.000 claims description 7
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims description 6
- 239000011241 protective layer Substances 0.000 claims description 6
- 239000010409 thin film Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000012790 adhesive layer Substances 0.000 claims description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 4
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 3
- 125000003700 epoxy group Chemical group 0.000 claims 3
- 230000003796 beauty Effects 0.000 claims 1
- 230000006641 stabilisation Effects 0.000 claims 1
- 238000011105 stabilization Methods 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 200
- 239000000243 solution Substances 0.000 description 162
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 153
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 120
- 239000003054 catalyst Substances 0.000 description 99
- 238000004817 gas chromatography Methods 0.000 description 74
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
- -1 photoinitiators Substances 0.000 description 69
- 229910052757 nitrogen Inorganic materials 0.000 description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 64
- 239000011541 reaction mixture Substances 0.000 description 57
- 239000000047 product Substances 0.000 description 53
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 51
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- 238000006243 chemical reaction Methods 0.000 description 50
- 238000003756 stirring Methods 0.000 description 47
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 46
- 238000012546 transfer Methods 0.000 description 41
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 38
- 230000015572 biosynthetic process Effects 0.000 description 35
- 239000012043 crude product Substances 0.000 description 34
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
- 230000001376 precipitating effect Effects 0.000 description 31
- 238000006116 polymerization reaction Methods 0.000 description 28
- 238000003786 synthesis reaction Methods 0.000 description 28
- 238000005481 NMR spectroscopy Methods 0.000 description 26
- 239000007787 solid Substances 0.000 description 26
- 239000012212 insulator Substances 0.000 description 25
- 235000019439 ethyl acetate Nutrition 0.000 description 24
- GETTZEONDQJALK-UHFFFAOYSA-N trifluorotoluene Substances FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 23
- MFGALGYVFGDXIX-UHFFFAOYSA-N 2,3-Dimethylmaleic anhydride Chemical compound CC1=C(C)C(=O)OC1=O MFGALGYVFGDXIX-UHFFFAOYSA-N 0.000 description 22
- 238000009472 formulation Methods 0.000 description 22
- 125000003118 aryl group Chemical group 0.000 description 21
- 239000003921 oil Substances 0.000 description 21
- 238000010992 reflux Methods 0.000 description 21
- 229920001577 copolymer Polymers 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000011521 glass Substances 0.000 description 18
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 17
- 125000000217 alkyl group Chemical group 0.000 description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 17
- 239000001301 oxygen Substances 0.000 description 17
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 16
- 238000004821 distillation Methods 0.000 description 16
- 229920001519 homopolymer Polymers 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- 239000000460 chlorine Substances 0.000 description 14
- 230000005855 radiation Effects 0.000 description 13
- VKQJCUYEEABXNK-UHFFFAOYSA-N 1-chloro-4-propoxythioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C(OCCC)=CC=C2Cl VKQJCUYEEABXNK-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 238000012545 processing Methods 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 239000010408 film Substances 0.000 description 11
- 229920002313 fluoropolymer Polymers 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 239000004811 fluoropolymer Substances 0.000 description 10
- 230000037230 mobility Effects 0.000 description 10
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- REBKUVYQFXSVNO-NSCUHMNNSA-N (3E)-1,1-dichloropenta-1,3-diene Chemical compound C\C=C\C=C(Cl)Cl REBKUVYQFXSVNO-NSCUHMNNSA-N 0.000 description 9
- 108091006146 Channels Proteins 0.000 description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000000654 additive Substances 0.000 description 9
- 239000012267 brine Substances 0.000 description 9
- 239000012153 distilled water Substances 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 9
- 239000000377 silicon dioxide Substances 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- 238000004528 spin coating Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000000137 annealing Methods 0.000 description 8
- 125000003710 aryl alkyl group Chemical group 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 229920003023 plastic Polymers 0.000 description 7
- 239000004033 plastic Substances 0.000 description 7
- 229920002959 polymer blend Polymers 0.000 description 7
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
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- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 6
- 150000002118 epoxides Chemical class 0.000 description 6
- 230000010354 integration Effects 0.000 description 6
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 5
- CGOJOQBYEAVATL-QPJJXVBHSA-N (e)-3-(4-methoxyphenyl)prop-2-enoyl chloride Chemical compound COC1=CC=C(\C=C\C(Cl)=O)C=C1 CGOJOQBYEAVATL-QPJJXVBHSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 238000005187 foaming Methods 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 239000002346 layers by function Substances 0.000 description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229940078552 o-xylene Drugs 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- QARVLSVVCXYDNA-UHFFFAOYSA-N phenyl bromide Natural products BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
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- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 4
- AZEGDYNKUSFFEJ-UHFFFAOYSA-N 2-octyloxirene Chemical compound CCCCCCCCC1=CO1 AZEGDYNKUSFFEJ-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
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- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 4
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
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- 238000004381 surface treatment Methods 0.000 description 4
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 3
- KCSFWQMXBIKNAC-UHFFFAOYSA-N 2-(4-bicyclo[2.2.1]hept-2-enyl)ethanamine Chemical compound C1CC2C=CC1(CCN)C2 KCSFWQMXBIKNAC-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 3
- ROZQDBBIHLJIMX-UHFFFAOYSA-N 3-(4-bicyclo[2.2.1]hept-2-enyl)propan-1-amine Chemical compound C1CC2C=CC1(CCCN)C2 ROZQDBBIHLJIMX-UHFFFAOYSA-N 0.000 description 3
- XVFJTUWWYKRTGI-UHFFFAOYSA-N 3-(4-bicyclo[2.2.1]hept-2-enyl)propanenitrile Chemical compound C1CC2C=CC1(CCC#N)C2 XVFJTUWWYKRTGI-UHFFFAOYSA-N 0.000 description 3
- ZSPTYLOMNJNZNG-UHFFFAOYSA-N 3-Buten-1-ol Chemical compound OCCC=C ZSPTYLOMNJNZNG-UHFFFAOYSA-N 0.000 description 3
- WCCUHUFYLYPMOC-UHFFFAOYSA-N 4-bicyclo[2.2.1]hept-2-enylmethanamine Chemical compound C1CC2C=CC1(CN)C2 WCCUHUFYLYPMOC-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004809 Teflon Substances 0.000 description 3
- 229920006362 Teflon® Polymers 0.000 description 3
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000005336 cracking Methods 0.000 description 3
- 239000013058 crude material Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
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- XBFJAVXCNXDMBH-UHFFFAOYSA-N tetracyclo[6.2.1.1(3,6).0(2,7)]dodec-4-ene Chemical compound C1C(C23)C=CC1C3C1CC2CC1 XBFJAVXCNXDMBH-UHFFFAOYSA-N 0.000 description 1
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- 229910052723 transition metal Inorganic materials 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/468—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics
- H10K10/471—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics the gate dielectric comprising only organic materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F32/00—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F232/00—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F32/00—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F32/02—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings
- C08F32/04—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings having one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L45/00—Compositions of homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic ring system; Compositions of derivatives of such polymers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/468—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics
- H10K10/478—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics the gate dielectric comprising a layer of composite material comprising interpenetrating or embedded materials, e.g. TiO2 particles in a polymer matrix
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/464—Lateral top-gate IGFETs comprising only a single gate
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/466—Lateral bottom-gate IGFETs comprising only a single gate
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/80—Constructional details
- H10K10/88—Passivation; Containers; Encapsulations
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Composite Materials (AREA)
- Thin Film Transistor (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Formation Of Insulating Films (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Electrodes Of Semiconductors (AREA)
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EP10009118 | 2010-09-02 | ||
EP10009118.0 | 2010-09-02 | ||
US37979910P | 2010-09-03 | 2010-09-03 | |
US61/379,799 | 2010-09-03 | ||
PCT/EP2011/004282 WO2012028279A1 (fr) | 2010-09-02 | 2011-08-26 | Couche isolante de grille destinée à des dispositifs électroniques |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2017027227A Division JP6334020B2 (ja) | 2010-09-02 | 2017-02-16 | 電子デバイス用のゲート絶縁層 |
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JP2013541191A JP2013541191A (ja) | 2013-11-07 |
JP2013541191A5 JP2013541191A5 (fr) | 2014-10-16 |
JP6097216B2 true JP6097216B2 (ja) | 2017-03-15 |
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JP2013526346A Active JP6097216B2 (ja) | 2010-09-02 | 2011-08-26 | 電子デバイス用のゲート絶縁層 |
JP2017027227A Active JP6334020B2 (ja) | 2010-09-02 | 2017-02-16 | 電子デバイス用のゲート絶縁層 |
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JP2017027227A Active JP6334020B2 (ja) | 2010-09-02 | 2017-02-16 | 電子デバイス用のゲート絶縁層 |
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US (2) | US9175123B2 (fr) |
EP (2) | EP2611841B1 (fr) |
JP (2) | JP6097216B2 (fr) |
KR (1) | KR101842735B1 (fr) |
CN (3) | CN105038069B (fr) |
DE (1) | DE112011102917T5 (fr) |
GB (1) | GB2497451A (fr) |
RU (1) | RU2013114414A (fr) |
SG (1) | SG187955A1 (fr) |
TW (1) | TWI618723B (fr) |
WO (1) | WO2012028279A1 (fr) |
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EP2436056B1 (fr) * | 2009-05-25 | 2016-08-03 | Basf Se | Dispositif électronique comprenant diélectriques organiques réticulables et son procédé de préparation |
EP2676978B1 (fr) | 2010-09-02 | 2015-06-24 | Merck Patent GmbH | Couche intermédiaire destinée à des dispositifs électroniques |
SG187955A1 (en) * | 2010-09-02 | 2013-03-28 | Merck Patent Gmbh | Gate insulator layer for electronic devices |
US9082981B1 (en) | 2012-01-16 | 2015-07-14 | Polyera Corporation | Curable polymeric materials and related electronic devices |
WO2013120581A1 (fr) | 2012-02-15 | 2013-08-22 | Merck Patent Gmbh | Couche de planarisation pour dispositifs électroniques organiques |
CN104245783B (zh) * | 2012-04-25 | 2017-12-12 | 默克专利股份有限公司 | 用于有机电子器件的堤岸结构 |
US9171961B2 (en) * | 2012-07-11 | 2015-10-27 | Polyera Corporation | Coating materials for oxide thin film transistors |
WO2014037076A1 (fr) * | 2012-09-04 | 2014-03-13 | Merck Patent Gmbh | Procédé de modification de surface de structures diélectriques dans des dispositifs électroniques organiques |
EP2898551B1 (fr) * | 2012-09-21 | 2020-04-22 | Merck Patent GmbH | Formulations de semi-conducteur organique |
TWI554534B (zh) * | 2012-09-25 | 2016-10-21 | 住友電木股份有限公司 | 含馬來醯亞胺之環烯烴聚合物及其應用 |
WO2014072016A1 (fr) * | 2012-11-08 | 2014-05-15 | Merck Patent Gmbh | Procédé de production de dispositifs électroniques organiques avec des structures de banque, structures de banque et dispositifs électroniques produits de cette manière |
US9035287B2 (en) * | 2013-02-01 | 2015-05-19 | Polyera Corporation | Polymeric materials for use in metal-oxide-semiconductor field-effect transistors |
US9786409B2 (en) * | 2013-06-27 | 2017-10-10 | Basf Se | Metathesis polymers as dielectrics |
US9356248B2 (en) * | 2013-08-16 | 2016-05-31 | Palo Alto Research Center Incorporated | Organic thin-film transistor |
KR101718941B1 (ko) | 2013-09-30 | 2017-03-22 | 주식회사 엘지화학 | 광반응기를 갖는 고리형 올레핀 화합물 및 광반응성 중합체 |
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JP6118287B2 (ja) * | 2014-03-26 | 2017-04-19 | 富士フイルム株式会社 | 半導体素子及び半導体素子の絶縁層形成用組成物 |
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US20180273722A1 (en) * | 2015-08-31 | 2018-09-27 | Zeon Corporation | Resin composition |
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US10429734B2 (en) | 2015-11-30 | 2019-10-01 | Promerus, Llc | Permanent dielectric compositions containing photoacid generator and base |
KR102465353B1 (ko) | 2015-12-02 | 2022-11-10 | 삼성전자주식회사 | 전계 효과 트랜지스터 및 이를 포함하는 반도체 소자 |
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CN109698276A (zh) * | 2018-12-27 | 2019-04-30 | 广州天极电子科技有限公司 | 一种薄膜晶体管器件及其制备方法 |
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CN105038069A (zh) | 2015-11-11 |
JP2013541191A (ja) | 2013-11-07 |
GB201303582D0 (en) | 2013-04-10 |
CN105038069B (zh) | 2017-10-17 |
CN103261250A (zh) | 2013-08-21 |
WO2012028279A9 (fr) | 2012-05-31 |
KR101842735B1 (ko) | 2018-03-27 |
WO2012028279A1 (fr) | 2012-03-08 |
US20120056183A1 (en) | 2012-03-08 |
TW201219432A (en) | 2012-05-16 |
US9647222B2 (en) | 2017-05-09 |
EP2676979B1 (fr) | 2016-07-13 |
CN104877292A (zh) | 2015-09-02 |
DE112011102917T5 (de) | 2013-09-05 |
EP2611841B1 (fr) | 2015-10-28 |
SG187955A1 (en) | 2013-03-28 |
US9175123B2 (en) | 2015-11-03 |
EP2676979A1 (fr) | 2013-12-25 |
RU2013114414A (ru) | 2014-10-10 |
KR20130114121A (ko) | 2013-10-16 |
US20150372246A1 (en) | 2015-12-24 |
JP6334020B2 (ja) | 2018-05-30 |
EP2611841A1 (fr) | 2013-07-10 |
TWI618723B (zh) | 2018-03-21 |
JP2017141446A (ja) | 2017-08-17 |
CN103261250B (zh) | 2016-11-09 |
GB2497451A8 (en) | 2013-06-19 |
GB2497451A (en) | 2013-06-12 |
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